55094-96-7

Basic information

• Product Name: (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE
• Synonyms: (S)-(+)-gamma-ethoxycarbonyl-gamma-butyrolactone,;(S)-(+)-4-ETHOXYCARBONYL-G-BUTYROLACTONE 98+%;(S)-(+)-4-Ethoxycarbonyl-ganna-butyrolactone;(S)-(+)-4-Ethoxycarbonyl-g-butyrolactone;ETHYL (2S)-5-OXO-2-TETRAHYDROFURANCARBOXYLATE;REF DUPL: (R)-(-)-Dihydro-5-(hydroxymethyl)furanone;(S)-(+)-γ-Ethoxycarbonyl-γ-butyrolactone ;2(3H)-Furanone, dihydro-5-(hydroxymethyl)-, (5R)-
• CAS NO: 55094-96-7
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 116.12
• Mol File: 55094-96-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 101-102 °C0.048 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.238 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00312mmHg at 25°C
• Refractive Index: n20/D 1.471
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE(55094-96-7)
• EPA Substance Registry System: (R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-FURANONE(55094-96-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 55094-96-7(Hazardous Substances Data)

Usage

General Description

(R)-(-)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone, also known as Dihydro-5-hydroxymethyl-2(3H)-furanone, is a chemical compound with a sweet, caramel-like odor and taste. It is commonly used as a flavoring agent and fragrance ingredient in various food and cosmetic products. The compound has been identified as a potent odor-active compound in a variety of natural products, including maple syrup, bread crust, and roasted coffee, and is also found naturally in fruits and vegetables. It has been shown to exhibit antioxidant and antimicrobial properties and may have potential applications in the food and pharmaceutical industries. Additionally, it has been investigated for its potential use as a bio-based building block for the synthesis of various valuable chemicals.

InChI:InChI=1/C7H10O4/c1-2-10-7(9)5-3-4-6(8)11-5/h5H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 141-78-6 ethyl acetate 
• 21461-85-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester 
• 1126-51-8 (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 5965-53-7 diethyl 2-ketoglutarate 
• 56-86-0 L-glutamic acid 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 13095-48-2 L-hydroxyglutaric acid 
• 69134-53-8 (+/-)-diethyl 2-hydroxypentandioate 
• 328-50-7 α-ketoglutaric acid 
• 64-17-5 ethanol 

Downstream Products

• 155768-47-1 -Ethyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 1309671-55-3 C₆₇H₆₃N₂O₅P 
• 1309671-42-8 (S)-1-(benzyloxy)-5-(pyren-1-yl)pentan-2-ol 
• 1309671-49-5 (S)-5-(benzyloxy)-1,1-(dipyren-1-yl)pentan-1,4-diol 
• 1309671-51-9 (S)-1-(benzyloxy)-5,5-(dipyren-1-yl)pentan-2-ol 
• 1309671-44-0 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5-(pyren-1-yl)pentan-2-ol 
• 1309671-53-1 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5,5-di(pyren-1-yl)pentan-2-ol 
• 1309671-47-3 C₅₁H₅₅N₂O₅P 

Relevant articles and documents

Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation

Random copolymers of ?-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-δ-valerolactone after hydrogenation form γ-hydroxy functionalized polyesters that degrade via the cyclization to γ-butyrolactone fragments without carboxylic acid formation.

Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid

An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.

Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo- 2-furancarboxylic acids and esters

Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned γ- lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd.